Our invention relates to the novel reaction products which are schiff base reaction products of alkyl anthranilates having the structure: ##STR5## wherein R" represents methyl or ethyl and ketones or aldehydes having the structure: ##STR6## wherein R' is hydrogen or methyl and R is one of the moieties: ##STR7## and the organoleptic uses thereof in augmenting or enhancing the aroma or taste of perfume compositions, colognes, perfumed articles, foodstuffs, chewing gums, toothpastes, medicinal products and chewing tobaccos; and in enhancing or augmenting the effect of deodorancy; as a maskant for malodors emanating from the auxilliary regions of mammalian species or as a maskant for malodors in detergent compositions or fabric softeners; and as a maskant for malodors for use in conjunction with other perfumery materials.
Inexpensive chemical compositions of matter which can provide concord grape, floral, orange blossom and neroli aroma and taste nuances for use in grape, neroli, mandarine and tangerine flavored foodstuffs are highly desirable in the food flavoring art as well as in the flavoring art for flavoring toothpastes, medicinal products, chewing gums and chewing tobaccos.
Furthermore, inexpensive chemical compositions of matter which can provide grape, animalic and rose aromas with hay-like, coumarinic, tonka absolute, honey and fatty topnotes and which are highly substantive and long-lasting are highly desirable in the art of perfumery. Many of the natural materials which provide such fragrances and contribute desired nuances to perfumery compositions as well as perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions and fabric softener articles are high in cost, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
Still more desirable are materials which can both provide useful fragrance effects including a high degree of substantivity and a long-lasting fragrance; and also provide a deodorancy effect wherey malodors can be masked by means of the use of the compound in, for example, compositions for application to the auxillary regions of mammalian species including human beings.
Reaction products of carbonyl-containing compounds and amine-containing compounds are well known in the art of flavoring and in the art of of perfumery. Thus, U.S. Pat. No. 4,618,501 issued on Oct. 21, 1986 discloses the flavoring of foodstuffs with alpha,beta-keto-amines and states that an alpha,beto-keto-amine having a nutty corn, cereal aroma may be used for flavoring compositions for foods having the structure. ##STR8## wherein R.sub.1, R.sub.2 and R.sub.3 are selected from the group consisting of a saturated or unsaturated alkyl straight or branched chain hydrocarbons having from 1-3 carbon atoms.
U.S. Pat. No. 3,625,710 issued on Dec. 7, 1971 discloses the use of aldimines as chocolate-like flavors which aldimines the resulting from the reaction product of amines and aldehydes, for example, N-isobutylidenefurfurylamine, N-isopentylidenefurfurylamine, N-isopentylideneisopentylamine.
Schiff bases are also well known in the art of perfumery. Thus, for example, Chemical Abstracts Volume 103, 1985, No. 123134z (Abstract of Japan Kokai No. 60/78951 discloses the use in perfumery of compounds having the structure: ##STR9##
Arctander "Perfume and Flavor Chemicals (Aroma Chemicals)", Volume II, published by the Author in 1969 discloses the organoleptic properties of the schiff base of methyl anthranilate and vanillin having the structure: ##STR10## thusly: